DE60005525T2 - 2-aminotetraline zur behandlung von glaukom - Google Patents
2-aminotetraline zur behandlung von glaukom Download PDFInfo
- Publication number
- DE60005525T2 DE60005525T2 DE60005525T DE60005525T DE60005525T2 DE 60005525 T2 DE60005525 T2 DE 60005525T2 DE 60005525 T DE60005525 T DE 60005525T DE 60005525 T DE60005525 T DE 60005525T DE 60005525 T2 DE60005525 T2 DE 60005525T2
- Authority
- DE
- Germany
- Prior art keywords
- iop
- chf
- eye
- glaucoma
- rabbits
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 208000010412 Glaucoma Diseases 0.000 title claims description 15
- LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- OMMYLOLVPCCZQZ-AWEZNQCLSA-N [(6s)-6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate Chemical compound C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1C[C@@H](NC)CC2 OMMYLOLVPCCZQZ-AWEZNQCLSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 abstract description 5
- 230000004410 intraocular pressure Effects 0.000 description 38
- TWTMQRXNAZGSCE-UHFFFAOYSA-N hydron;[6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate;chloride Chemical compound Cl.C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1CC(NC)CC2 TWTMQRXNAZGSCE-UHFFFAOYSA-N 0.000 description 27
- 241000283973 Oryctolagus cuniculus Species 0.000 description 17
- 210000001508 eye Anatomy 0.000 description 17
- 229940079593 drug Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000003889 eye drop Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XYLJNLCSTIOKRM-UHFFFAOYSA-N Alphagan Chemical compound C1=CC2=NC=CN=C2C(Br)=C1NC1=NCCN1 XYLJNLCSTIOKRM-UHFFFAOYSA-N 0.000 description 5
- 206010015946 Eye irritation Diseases 0.000 description 5
- 229960003679 brimonidine Drugs 0.000 description 5
- 231100000013 eye irritation Toxicity 0.000 description 5
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 229940012356 eye drops Drugs 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LSHRDKPBUUXBAF-UHFFFAOYSA-N 6-(dimethylamino)-5,6,7,8-tetrahydronaphthalene-1,2-diol Chemical compound C1=CC(O)=C(O)C2=C1CC(N(C)C)CC2 LSHRDKPBUUXBAF-UHFFFAOYSA-N 0.000 description 3
- 210000001742 aqueous humor Anatomy 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002876 beta blocker Substances 0.000 description 3
- 229940097320 beta blocking agent Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000008055 phosphate buffer solution Substances 0.000 description 3
- 239000000902 placebo Substances 0.000 description 3
- 229940068196 placebo Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 206010030348 Open-Angle Glaucoma Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 229960002376 chymotrypsin Drugs 0.000 description 2
- OCUJLLGVOUDECM-UHFFFAOYSA-N dipivefrin Chemical compound CNCC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 OCUJLLGVOUDECM-UHFFFAOYSA-N 0.000 description 2
- 229960000966 dipivefrine Drugs 0.000 description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
- 208000030533 eye disease Diseases 0.000 description 2
- 210000000744 eyelid Anatomy 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- JWLJBTDXCBIGBW-UHFFFAOYSA-N 6-(dimethylamino)-5,6,7,8-tetrahydronaphthalene-2,3-diol Chemical compound OC1=C(O)C=C2CC(N(C)C)CCC2=C1 JWLJBTDXCBIGBW-UHFFFAOYSA-N 0.000 description 1
- ASXGAOFCKGHGMF-UHFFFAOYSA-N 6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol Chemical compound OC1=C(O)C=C2CC(N)CCC2=C1 ASXGAOFCKGHGMF-UHFFFAOYSA-N 0.000 description 1
- KFQYTPMOWPVWEJ-UHFFFAOYSA-N 6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1CC2=C(O)C=CC=C2CC1N(CCC)CCC1=CC=CS1 KFQYTPMOWPVWEJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- 201000002862 Angle-Closure Glaucoma Diseases 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- RNLAYPARPUAAJR-UHFFFAOYSA-N C(CC)NC1CC2=CC=C(C=C2CC1)NC(=O)O Chemical compound C(CC)NC1CC2=CC=C(C=C2CC1)NC(=O)O RNLAYPARPUAAJR-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical class ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 206010018325 Congenital glaucomas Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 206010012565 Developmental glaucoma Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- OMMYLOLVPCCZQZ-UHFFFAOYSA-N [6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate Chemical class C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1CC(NC)CC2 OMMYLOLVPCCZQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 108010027597 alpha-chymotrypsin Proteins 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 230000002562 anti-bronchospastic effect Effects 0.000 description 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 1
- 229960002610 apraclonidine Drugs 0.000 description 1
- IEJXVRYNEISIKR-UHFFFAOYSA-N apraclonidine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NCCN1 IEJXVRYNEISIKR-UHFFFAOYSA-N 0.000 description 1
- 230000004509 aqueous humor production Effects 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000004397 blinking Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 231100000478 corneal permeability Toxicity 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 230000004406 elevated intraocular pressure Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002357 osmotic agent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000002504 synaptic vesicle Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI991713 | 1999-07-30 | ||
| IT1999MI001713A IT1313583B1 (it) | 1999-07-30 | 1999-07-30 | Derivati 2-amminotetralinici per la terapia del glaucoma. |
| PCT/EP2000/007184 WO2001008667A2 (en) | 1999-07-30 | 2000-07-26 | 2-aminotetralin derivatives for the therapy of glaucoma |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60005525D1 DE60005525D1 (de) | 2003-10-30 |
| DE60005525T2 true DE60005525T2 (de) | 2004-04-22 |
Family
ID=11383465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60005525T Expired - Fee Related DE60005525T2 (de) | 1999-07-30 | 2000-07-26 | 2-aminotetraline zur behandlung von glaukom |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6953813B1 (it) |
| EP (1) | EP1200079B1 (it) |
| JP (1) | JP2003505499A (it) |
| CN (1) | CN1170532C (it) |
| AT (1) | ATE250413T1 (it) |
| AU (1) | AU778148B2 (it) |
| CA (1) | CA2379778A1 (it) |
| CZ (1) | CZ2002358A3 (it) |
| DE (1) | DE60005525T2 (it) |
| ES (1) | ES2207544T3 (it) |
| HK (1) | HK1048594A1 (it) |
| HU (1) | HUP0202098A3 (it) |
| IT (1) | IT1313583B1 (it) |
| NO (1) | NO20020475L (it) |
| PL (1) | PL364794A1 (it) |
| WO (1) | WO2001008667A2 (it) |
| ZA (1) | ZA200200787B (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL152751A0 (en) * | 2000-05-12 | 2003-06-24 | Chiesi Farma Spa | Optically active 2-aminotetralin derivatives, the processes for the preparation thereof and the therapeutical use of pharmaceutical compositions containing them |
| US20020198209A1 (en) * | 2001-05-03 | 2002-12-26 | Allergan Sales Inc. | Compositions having enhanced pharmacokinetic characteristics |
| KR20080065704A (ko) | 2005-11-09 | 2008-07-14 | 콤비네이토릭스, 인코포레이티드 | 의학적 이상의 치료 방법들, 조성물들, 및 키트들 |
| US7829587B2 (en) * | 2008-01-09 | 2010-11-09 | Allergan, Inc. | Substituted 2-aminotetralin derivatives as selective alpha 2B agonist |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA794872B (en) * | 1978-09-20 | 1980-11-26 | Schering Corp | A phenylalkylaminoethylsalicylamide,its preparation and pharmaceutical compositions containing it |
| IT1218322B (it) * | 1982-06-10 | 1990-04-12 | Chiesi Farma Spa | Derivati di 1,2,3,4-tetraidronaftalene,procedimento di preparazione e relative composizioni farmaceutiche |
| US5236907A (en) * | 1988-10-01 | 1993-08-17 | R-Tech Ueno Ltd. | Ocular hypotensive agents |
| US5314916A (en) * | 1993-04-19 | 1994-05-24 | Alcon Laboratories, Inc. | B2 adrenegic agonists and use thereof in the treatment of glaucoma |
| IT1275935B1 (it) | 1995-03-17 | 1997-10-24 | Chiesi Farma Spa | Derivato di aminotetralina per la terapia di malattie cardiovascolari |
-
1999
- 1999-07-30 IT IT1999MI001713A patent/IT1313583B1/it active
-
2000
- 2000-07-26 CN CNB008108676A patent/CN1170532C/zh not_active Expired - Fee Related
- 2000-07-26 CA CA002379778A patent/CA2379778A1/en not_active Abandoned
- 2000-07-26 HK HK03100759.8A patent/HK1048594A1/zh unknown
- 2000-07-26 HU HU0202098A patent/HUP0202098A3/hu unknown
- 2000-07-26 CZ CZ2002358A patent/CZ2002358A3/cs unknown
- 2000-07-26 JP JP2001513397A patent/JP2003505499A/ja active Pending
- 2000-07-26 AT AT00956296T patent/ATE250413T1/de not_active IP Right Cessation
- 2000-07-26 PL PL00364794A patent/PL364794A1/xx not_active Application Discontinuation
- 2000-07-26 US US10/030,114 patent/US6953813B1/en not_active Expired - Fee Related
- 2000-07-26 AU AU68293/00A patent/AU778148B2/en not_active Ceased
- 2000-07-26 ES ES00956296T patent/ES2207544T3/es not_active Expired - Lifetime
- 2000-07-26 WO PCT/EP2000/007184 patent/WO2001008667A2/en not_active Ceased
- 2000-07-26 EP EP00956296A patent/EP1200079B1/en not_active Expired - Lifetime
- 2000-07-26 DE DE60005525T patent/DE60005525T2/de not_active Expired - Fee Related
-
2002
- 2002-01-29 ZA ZA200200787A patent/ZA200200787B/en unknown
- 2002-01-29 NO NO20020475A patent/NO20020475L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1048594A1 (zh) | 2003-04-11 |
| HUP0202098A2 (en) | 2002-10-28 |
| ZA200200787B (en) | 2003-03-26 |
| IT1313583B1 (it) | 2002-09-09 |
| CN1170532C (zh) | 2004-10-13 |
| WO2001008667A3 (en) | 2001-06-07 |
| US6953813B1 (en) | 2005-10-11 |
| EP1200079A2 (en) | 2002-05-02 |
| CN1364081A (zh) | 2002-08-14 |
| WO2001008667A2 (en) | 2001-02-08 |
| AU6829300A (en) | 2001-02-19 |
| DE60005525D1 (de) | 2003-10-30 |
| ITMI991713A0 (it) | 1999-07-30 |
| ES2207544T3 (es) | 2004-06-01 |
| ITMI991713A1 (it) | 2001-01-30 |
| ATE250413T1 (de) | 2003-10-15 |
| PL364794A1 (en) | 2004-12-13 |
| CA2379778A1 (en) | 2001-02-08 |
| AU778148B2 (en) | 2004-11-18 |
| HUP0202098A3 (en) | 2003-08-28 |
| NO20020475L (no) | 2002-03-13 |
| NO20020475D0 (no) | 2002-01-29 |
| EP1200079B1 (en) | 2003-09-24 |
| CZ2002358A3 (cs) | 2002-04-17 |
| JP2003505499A (ja) | 2003-02-12 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |